Wrestlers Who Bet On Themselves & Lost

The term “betting on yourself” in wrestling typically applies to wrestlers taking a risk. Cody Rhodes leaving WWE and then leaving AEW showed the blueprint for success in this context. Mustafa Ali becoming the hottest ticket mover on the independent circuit showed his approach to be a traveling free agent paying off.

5 Big Risks WWE Took In The 2010s That Paid Off (& 5 That Backfired)

Not every risk WWE took in the 2010s ended up working out, with some of them backfiring and having an adverse impact.

Unfortunately, not every wrestler trying something new or giving up a stable promotion to prove themselves will see it working out. There have been instances of a talent thinking they were about to hit a home run before striking out. Each of the following wrestlers bet on themselves and lost in various ways.

DDP Was Rare Top WCW Star To Join WWE During The Invasion

Most Other WCW Main Eventers Let Contracts Run Out

Debuted In Horrible WWE Storyline Stalking Undertaker's Wife
Getting Buried In First WWE Feud Completely Ruined His Appeal
WWE Made WCW's Second Biggest Invasion Star Look Like A Joke

WWE dropped the ball with the Invasion storyline for many reasons, but one problem was outside of their control. WCW’s wrestlers with guaranteed contracts had the option to let their contracts run out making huge money or getting out of it to sign a new WWE deal.

WWE’s Invasion: 6 WCW Wrestlers Who Got Booked Poorly (& 4 Who Were Booked Well)

The Invasion is considered one of the worst storylines of all time by fans. Most WCW wrestlers weren't booked well in WWE, while a select few were.

Names like Hulk Hogan, Sting, Goldberg and Kevin Nash missed the Invasion letting their deals run out. Diamond Dallas Page and Booker T were the two biggest WCW stars to join WWE and ditch their deals. Booker became a star, but DDP barely did nothing of note, with WWE booking him poorly. A debut feud stalking Undertaker's wife ruined Page's entire WWE run.

Ultimate Warrior Believed In His Own Hype Too Much

Abusing Power In WWE Led To The Self-Destruction Of His Own Career

Started To Become Unreliable When Getting Main Event Status
Multiple Ugly Endings With WWE Saw Warrior Betting On Self
WCW Tenure Feuding With Hulk Hogan Killed Remaining Name Value

WWE started to lose faith in Ultimate Warrior as one of the faces of the company when he tried to use his power too much. Warrior making financial demands and backing out of agreed deals showed he was not going to be reliable.

There were multiple instances of Warrior butting heads with WWE management over ridiculous things to end a few of those stints poorly. Warrior bet on himself by continuing the cycle and going to WCW, but he just ruined whatever name value he had left with such a bad tenure outside of WWE.

EC3 Betting On His Own Promotion Was A Swing & Miss

Control Your Narrative Ruined EC3’s Reputation In Wrestling

Wanted To Take Bigger Risks When Getting Released From WWE
Starting His Own Promotion Turned Out To Be A Huge Mistake For EC3
Control Your Own Narrative Becoming Punch Line Ruined His Value

EC3’s second WWE tenure ended in huge disappointment after fans had higher hopes thanks to his TNA main event success. Most assumed EC3 would just head back to Impact Wrestling when he was released, but he decided to bet on himself.

Control Your Narrative was a new promotion started by EC3 with the hopes of making it on his own. The promotion received negative attention for its rules and embarrassing first few shows. EC3 rarely gets much attention these days unless you watch NWA or hot take YouTube shows religiously.

Disco Inferno Refused To Lose To Jacqueline In WCW

Eric Bischoff Made Him Lose To Her When Returning From Absence

Left Job Over Refusing To Lose Match Against Female Wrestler
Couldn't Land WWE Job During Time Away From WCW
Returned & Agreed To Job To Jacqueline To Get Back His Job

Intergender wrestling was a rare concept in the 1990s with WCW testing it out. The idea for Jacqueline defeating Disco Inferno was pitched since she was considered the most credible female talent, and he was a lower card comedy act.

Disco refusing to lose to a woman saw him losing his job and betting on himself. There were rumors of WWE being interested in Inferno playing Rockabilly, but nothing came of it. Disco went right back to WCW after a few months on the unemployment list and agreed to put over Jacqueline to return.

Bobby Fish Couldn’t Find Home In WWE Nor AEW

Trying To Continue Career Without Undisputed Era Teammates

Left AEW Due To Wanting More Money In Longer Deal
Lost A Lot Of Momentum During Embarrassing TNA Promo
Has Been Relatively Quiet Since Betting On Himself

WWE releasing Bobby Fish saw him landing in AEW as a natural fit to work with Adam Cole and Kyle O’Reilly. Fish felt he didn’t get a fair contract offer to stay and chose to leave and hit the free agency market.

Outside of an embarrassing viral video from an Impact appearance and news to return to MLW, Fish has been relatively quiet. Roderick Strong joining AEW and aligning with Cole has more than enough bodies there for that story to show why Fish was expendable.

Raven Regretted Asking For Release During Wild WCW Meeting

Eric Bischoff Offered Unhappy Raven Chance To Get Out Of Contract

There was heat between Eric Bischoff and Raven after the latter did radio interviews criticizing WCW’s creative direction. Bischoff was already upset at Raven when he had his infamous meeting offering a release to anyone unhappy.

10 WCW Backstage Stories That Blow Our Minds

Since WCW ended, wild behind-the-scenes tales have come out. Superstars shared gossip about their wrestling days in and out of the ring..

Raven felt singled out and was the only person to get granted his release that night. Neither a return to ECW nor a WWE deal worked to Raven’s advantage. Future interviews saw Raven admit he made a mistake and would have likely made more money spending the rest of WCW’s existence there.

Madusa Throwing Belt In Trash Was A Mistake

She Thought She’d Spend The Rest Of Her Career With WCW

Burned WWE Bridges Throwing Belt In Trash For WCW & Eric Bischoff
Realized She Made Mistake With WCW's Weak Women's Division
WWE Blacklisted Her For Two Decades Until Finally Making Peace

WCW scored a major move adding Madusa to the roster both for a top female star returning from their past and for being the WWE Women’s Champion when her deal expired. Eric Bischoff talked Madusa into bringing the belt and throwing it in a trash can on WCW TV.

Madusa bet on herself by doing that since she knew it would cause backlash from WWE. The wrestling career of Madusa ended when her WCW tenure did. WWE didn’t bring Madusa back in any way until two decades later with a Hall of Fame induction in 2015 to bury the bad blood.

Chris Harris Going For His WWE Dreams Backfired

Left Great Spot In TNA For Career-Killing WWE ECW Run

Wanted To Join WWE For Major Singles Opportunity
Didn't Want To Wait For James Storm To Jump With Him
Braden Walker WWE Run Ended Any Chance Of Success

TNA made Chris Harris one of their first true homegrown stars in the early years. Harris and James Storm broke out as the tag team America’s Most Wanted, but they split up to chase singles careers. TNA couldn’t convince Harris to say when his deal ended, despite pushing him more than Storm.

WWE wanted Harris to be a rare TNA star that joined the company and renamed him Braden Walker. The ECW brand witnessed this chapter being a failed stint that ruined his career completely. Storm claims that WWE wanted them both if Harris waited longer, but he wanted the singles run that flopped.

Vince Russo Leaving WWE Killed His Legacy

WCW & TNA Runs Make Fans Overlook His Attitude Era Success

Russo Leaving WWE Was A Major Risk While The Attitude Era Was Hot
Horrible WCW Tenure Ruined All Goodwill From His Time In WWE
TNA Added More Negative Chapters To Hurt Russo's Legacy

Vince Russo is rightfully viewed as one of the most polarizing minds in wrestling history. However, even critics of Russo would admit his legacy would be much different if retired at the end of his WWE run. Russo surely did bet on himself leaving a lead writer spot while WWE was on fire.

The bet that Russo could help WCW failed badly with reasons both in and out of his control leading to disaster. Russo is remembered more negatively by most in the wrestling world for the awful WCW and TNA stints after leaving WWE.

Alberto Del Rio Getting His WWE Release Started His Demise

Things Just Got Worse For Del Rio Every Step After Controversial WWE Exit

Demanded Release From WWE After Violating Wellness Policy
Being Unreliable For Impact Wrestling Ruined His Reputation
Wants To Work For WWE Again

Both of Alberto Del Rio’s WWE stints ended in shocking fashion, but the second one was a bigger deal. Del Rio and Paige aka Saraya both failed the Wellness Policy, with Alberto claiming that WWE was trying to set him up and demanding a release.

WWE releasing Alberto just led to his career falling apart in various ways. Negative stories about him allegedly abusing Saraya and professional disasters like his Impact Wrestling stints doomed Del Rio. The sad twist is that Alberto expresses a desire to work with WWE again after betting on himself by burning that bridge.

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